Eliot Path, Skyline to Hancock, Jeffries, Dalton, Raccoon Hollow (Blue Hills Reservation)

Eliot Path, Skyline to Hancock, Jeffries, Dalton, Raccoon Hollow (Blue Hills Reservation)

Hike Type: Criss-crossing Loop

Distance: 5.79 miles

Elevation: 1,145 feet

My Time: 2 hours

Book Time: 3 hours, 28 minutes

Parking: Ample parking at Trailside Museum
Hiking Challenges: Great Blue Hill Summits, Trail Trace the Blue Hills 2

The Hike 

I was feeling absolutely desperate for a redemption after yesterday's unpleasant hike. I decided to head down to the Blue Hills after my second to last Monday of the school year to hopefully get what I needed! The drive, naturally, had "heavier than usual traffic," and I was at the trailhead just before 3:40pm. I wasn't feeling like doing a Skyline Loop, so I figured I'd start on the Eliot Path and see where the wind took me. It was 81 and partly cloudy with an intermittent breeze, but the humidity was low and it was NICE. I guess summer can be okay?

The rocks on Eliot Path had a solid dusting of pollen on them, which made them slippery. I made my way up, visiting the ski spur before crossing the Summit Road. The ski trails were grown-in, so I cut through the woods to get both forks of the spur, hiking over many, MANY deer prints all around! I crossed the road and heard the first cicada of summer!

Just before Eliot Circle, I passed a woman in floral skinny jeans with a vastly different floral blouse on. She was actually super friendly, and told me about a family of deer she saw up here a few days ago, implying this floral-on-floral hiking fit was 100% on purpose - spectaular!

I played a little bit of Pokemon Go on Eliot Circle, and followed it all the way to the gravel path to the summit (counter clockwise). The area closest to the ski area was growing in, but by no means overgrown (yet). I worked my way up to the summit, potentially seeing a new gray bird (Update Pending)?

From the summit, I crossed the road and noticed a little path to a parking area, and then another path with a "no bike" plackard by DCR, so I decided to follow it! It was actually a wide, well-beaten path to the backside of the Eliot Tower pavillion - fun! I decided I'd hike the Skyline North to Hancock Hill, hit the Circle Trail, and then see what would happen after that. It was a beautiful day, and I was feeling good!

I made my way down to Wildcat Notch and found a DCR officer in an ATV looking lost or stuck on Puddle Path? She was on the phone with someone holding a map, and then slowly backed out... I wonder where she was heading? I crossed paths with a a family on Wolcott Hill that looked dressed for Houghton's Pond. 

The berries of all sorts were starting to grow in on Wolcott and there was more of that wonderful breeze. I was sweaty for sure, but I did NOT want to die, which was huge! As I descended into Downtown Crossing, I heard the ATV driving away again...

I worked my way up Hemenway, passing a cool snake shed on some of the rocks. I continued along, climbing up after Breakneck Ledge Path and then snaking my way through another family that was coming down towards Circle Trail. 

Up on Hancock's ridge, I noticed some of the blueberriers were starting to turn purple, and some even blue!! I hit the circle of the Circle Trail, which was a little grown-in, but I had my first handful of ripe blueberries of the season! Maybe summer isn't as awful after all...

I continued back into the woods on Circle Trail, enjoying more of a breeze as I made my way down towrads JeffriesTrail. I noticed some horse poop, which must have been a mistake becuase Circle Trail is a horse dead-end. The stream to Jeffries was absolutely bone dry, and higher up, the blueberries were still green. Good to know - Hancock's will be ripe by next week, but Jeffries' are probbaly another week behind. 

I made my way back up Hemenway Hill, and then I descended again on Hemenway Hill Path before hiking on the absolutely delightful Five Corners Path back to Downtown Crossing. I think I traditionally hike this stretch in spring during the melting season, so I've only ever been miserable on this stretch, so this was a win!

I hiked on the Skyline Trail back up Wolcott, trying to pick up the pace because the family was right behind me, and then I went down Dalton Path to get some more new trails. There are some bore holes on rocks near a swamp on Dalton, I wonder what that's all about? I guess either science or an old settlement, but this just feels like a strange place for it.

I hiked up Raccon Hollow, swatting away the only relentless bugs of the day, and then hiked the rest of Eliot Circle to finish out my second summit! I followed the road for a bit to play a little more pokemon, and then made my final descend on Eliot Path back to the car. This was the hike I absolutely needed!

Step-by-Step

- Park at Trailside Museum.

- Start hike on Eliot Path.

- Before road, turn right to ski area spurs.

- Return to Eliot Path at 1051.

- At 1055, turn right onto Eliot Circle.

- After 1030, turn left onto gravel path to summit.

- From summit, continue onto Summit Road.

- At path, turn right.

- Walk across parking lot, continuing onto unmapped path in woods (marked by a no-bike DCR plackard).

- At terminus, walk through Eliot Tower towards 1063.

- At 1063, turn left onto Skyline Trail North.

- After summiting Hancock Hill, hike the circle of Circle Trail clockwise, then continue on Cirlce Trail towards 1180.

- At 1180, continue onto Breakneck Ledge Path.

- At 1185, turn left onto Base Path.

- At 1182, turn left onto Jeffries trail.

- At 1150, turn around.

- At 1154, turn left onto Hemenway Hill Path.

- At 1140, turn left onto Five Corners Path (green).

- At 1141, turn right onot Skyline Trail.

- At 1117, turn right onto Dalton Path.

- At terminus, turn left onto Wildcat Notch Path.

- At 1092, turn right onto Raccoon Hollow Path.

- At terminus, turn left onto Eliot Circle.

- Before 1030, turn right onto gravel path to summit.

- From summit, continue onto Summit Road.

- Follow Summit Road.

- At 1051, turn left onto Eliot Path.

- Return to car.

Blue Hills Reservation Map

Photo Album

Chickatawbut Hill, Bouncing Brook Path, Skyline Trail Loop (Blue Hills Reservation)

Chickatawbut Hill, Bouncing Brook Path, Skyline Trail Loop (Blue Hills Reservation)

Hike Type: Mostly Lollipop Loop

Distance: 4.54 miles

Elevation: 640 feet

My Time: 1 hour, 39 minutes

Book Time: 2 hour, 35 minutes

Parking: Room for 20-30 cars at Chickatawbut Overlook.
Hiking Challenges: 52 Hike Challenge 2026, Trail Trace the Blue Hills 2, Blue Hills Grid

The Hike 

I made my way back to the Blue Hills after school, suffering through another afternoon of "unusually heavy traffic." The inspiration for this hike was the Blue Hills Grid that I've been "working" on for years now, plus my second Trail Trace map. I had field day today, so I had been outside for a lot of the afternoon, but I was excited to keep the momentum going! It was 78 degrees out and overall pretty pleasant!

I made my way into the woods and up to the tower before following the yellow blazes counter-clockwise. I stopped for a quick potty break and managed to pee on my hip belt strap... Ugh. I worked my way up Thayer Path, which was grassy up around the summit fence (I had tick anxiety). I went down Carve Path, which had it's trademark giant rock piles that I've always been wildly curious about. 

I then made my way down onto the Bouncing Brook Path, which I'd be following for a while. It was darker and more humid down there, and I was following horse prints for most of the walk. I passed some lovely purple flowers, which were lesser periwinkle, not violets. I passed a really nice stone wall I hadn't noticed before just before the junction with Lee Path, and then a lady slipper just before the junction with Sassaman! Just kidding! At the junction with Curve Path! I missed a turn! That's fine, my hike was going to be a bit longer.

Everytime I'm hiking these interior Chickatawbut trails I'm reminded of how long they feel - it must be because there's a thinner density of trails in this area, or something. The bugs were present but not much of a bother as long as I kept on moving. I worked up Wampatuck Path and then the Pocapawmet Path to join the Skyline Trail!

I don't think I have traveled this direction on the Skyline Trail since a hike with Gen and Wylie in the winter of 2021 or 2022 - it's been a minute! I passed a super cute eastern towhee on my way up Broken Hill #4 and then maneuvered the rockiness that surrounds #3 - there were baby blueberries! A deer magically lept across the trail as I was climbing up #2 and there were some young rock harlequin flowers at the top. 

The climb up #1.5 was also rockier than I had realized traveling in the other direction, and I found myself wondering how different the forest would be on #1 in 10, 20, 50 years since the last fire. It looked like most of the pines were dead/dying and the undergrowth was growing in strong! I passed more pink lady slippers and rock harlqeuins as I descended #1, and then I started my climb up Nahanton.

The climb up the Chickatawbut Ridge was actually more gradual than I was emotionally ready for. I climbed on up Nahanton, past some more baby blubes, and found myself wondering yet again about the old foundation-like things. I admired the stone steps up Kitchamakin and suffered through the brush to reach the true top of Fenno Hill before making my way up to Chickatawut Hill. I descended via Stowe Path and made it back to the car - this was officially a zero-person hike! I dusted the pollen off of myself (literally) and heard a barrel owl calling somewhere on the other side of the road.

Step-by-Step

- Park at Chickatawbut Overlook.

- Start hike on Tower Path (yellow).

- At 3075, turn left onto Sassaman Notch Path (yellow).

- At second jct., turn right onto Thayer Path.

- At fence, turn left.

- At second jct., continue right onto Skyline Trail (blue).

- At 3065, turn left onto Carve Path.

- At 3051, turn left onto Bouncing Brook Path (red). 

- At 3152, turn left onto Wampatuck Path.

- At 3171, turn around and turn right onto Pocapawmet Path (unmapped).

- At terminus, turn left onto Skyline Trail (blue).

- At Chickatawbut Hill, turn right onto Thayer Path, then turn right again onto Stowe Path.

- At jct., turn left to stay on Stowe Path.

- At terminus, turn left onto Sassaman Notch Path (yellow).

- At 3075, turn right onto Tower Path (yellow).

- Follow Tower Path back to car.

Blue Hills Reservation Map

Photo Album

Red Dot and Skyline Loops via Trailside Museum (Blue Hills Reservation)

Red Dot and Skyline Loops via Trailside Museum (Blue Hills Reservation)

Hike Type: o-O Loop

Distance: 4.97 miles

Elevation: 1,220 feet

My Time: 1 hour, 46 minutes

Book Time: 3 hours, 5 minutes

Parking: Ample room at Trailside Museum
Hiking Challenges: 52 Hike Challenge 2026, Trail Trace the Blue Hills 2, Great Blue Hill Summits

The Hike 

Happy Pride Month! It was time to officially begin my second Trail Trace the Blue Hills Map! I had a dreadfully sleep drive with "heavier than usual traffic," landing at the Trailside Museum at 3:35. There were very few cars, which brought me joy! I was planning on just doing a fitness hike with a possible detour to get the full red-circle route for my new map, we'll see! It was sunny, 62 degrees, and there was a light breeze. It was lovely!

Somebody unfortuantely got started right before me, but I had to pull off to pee anyway. I eventually caught up and passed him and continued my way up. There were a bunch of leaves on the ground after Saturday's storm. My legs were in a weird mood, feeling a bit like a baby deer learning to walk. I couldn't really get a rhythm together on my climb. Thankfully, I could hear a bunch of eastern towhees, which made it feel better!

I passed a bunch of white daisies after summiting the first time. The work on the summit area has been continuing, with another widening of the Eliot Circle for trucks (I assume). I made my way onto the Skyline Trail North, admiring how shaded it is this time of year. Naturally, I was gassy on this hike, and at one point I made three stomps, farting on each stomp, and the pitches of each fart were different and accurately mimiced the final three notes of the University of Massachusetts Minuteman Marching Band's rendition of Frank Sinatra's My Way - it was remarkable.

I worked my way up and over Wolcott, Hemenway, and then Hancock. My body was just feeling tired and heavy, maybe because I had wine before bed last night? I passed some beautiful blue jays coming down Hancock Hill and I was simply not emotionally ready for the climb up Houghton. Thankfully, the climb did not humble me as badly as I thought it would. I did gas me out, but I was not passing away.

The leaves made the Skyline Trail super dark at the first stream crossing, and to my absolute delight I found some lady slippers between 1123 and the Five Corners Path!! This is where I usually find them this time of year, so I was just elated.

The second stream crossing was fully dried up and I noticed a path straight ahead before the crossing to what looks like a cave? I had never noticed it before... interesting! I made a note of it, being too lazy to investigate. I zig-zagged up to the final headwall, suffered on up, and then continued up along the shoulder for the final push, which always feels longer than I am ready for!

I listened to the northern house wrens at the summit (thank you, Merlin!) and decided to follow the other half of the red loop for my trip down, which was lovely. The swamp along the trail was mostly dry, and it looked like DCR is working on formally closing a few of the abandoned trails in that area. My final stretch of trail was cheered on by a friendly Robin, which was just lovely.

Step-by-Step

- Park at Trailside Museum.

- Start hike on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle.

- At summit road, turn left.

- At jct., turn right.

- At summit, hike around observatory clockwise, following gravel path.

- At terminus of gravel path, turn left onto Skyline Trail (blue).

- At 1063, turn right onto Skyline Trail North.

- At Hillside St., turn right onto Hillside Street.

- At jct.,. turn right onto Skyline Trail South.

- At 1066, turn left onto Eliot Circle/Skyline Trail.

- At gravel path, turn right onto Gravel Path.

- At summit, continue straight and hike spur towards ski trail.

- At jct., turn right onto Eliot Cirlce.

- After 1055, turn left onto Raccoon Hollow Path (red).

- At 1082, turn left onto Cliff Trail (red).

- Cross Summit Road, continue onto Trailside Path (red).

- Follow red dots back to car.

Blue Hills Reservation Map

Photo Album